There are some great comments and pictures posted here, thanks so much my fine people. And I really appreciate the mock-ups groveraxle. :) This exterior has become quite stressful to me. So much more comfortable with interiors. I have some things to go with here but in the end I'll probably just bite the bullet and hire a designer...lol.

Thank you! And maybe... I’m afraid to go too white tho. And I’m not sure what to do with the detail around the windows. I love the tone on tone look, like in this picture. But I’m not sure I can achieve that look since I don’t hv shutters. Can I paint the detail around the windows in a slightly darker tone and achieve something close to this? Not sure...

I'd go with a creamy white, as you said. I wouldn't pick anything too bright/stark white (especially on the garage door), since your other home colors are more earthy. It's hard to see on a computer, but I assume White Duck is just that, a slighter warmer white. We painted our trim SW Alabaster for the same reason, and love it.

Some things to understand about exterior siding: 1. The siding is the first water shedding surface - but it's not the final. There should be Tyvek or similar (Tyvek is actually superior to most) that is the drainage plane. 2. Caulk should not be relied upon to maintain waterproofing. It will always dry, crack, etc. So, the answer to your brick issue: I would use L shaped flashing from the wall at the brick line to a point completely covering the gap between the brick and the wall plus 3/4" or more. I'd seal the underside of that flashing with clear silicone caulk to the brick to prevent water going under the flashing. Then Tyvek on the walls to overlap the flashing. The brickmould trim would go over the top of the L flashing - hiding most of it - and Z flashing would be integrated into that. The siding and the flashing is the first water shedding and the Tyvek and the next layer of flashing is the final drainage plane. You have a Palladian window upstairs. Google it to see good examples. Done properly - it shouldn't look like discrete units - it should hold together. The installers didn't really build it that way - so I'm not sure how that will work if you make the trim wider. Sketch it out to scale and see how it looks with wider trim.